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gilligan 

A girl dat looks good and dats a freak as well.
Hey Girl, is you gill?
Hey dat girl gill as hell!
gilligan by jp January 26, 2005

Gilligan 

When you are totally trying to be nice to someone, but you fuck it all up.
"He fixed Ginger's skateboard, for free from what I hear."
"Ginger can't skate anymore, she's in a wheelchair!"
"You didn't let me finish- from what I hear he left it on her back porch as a surprise."
"That's how she ended up in a wheelchair? What a Gilligan!"
Gilligan by Trans-AmIam November 2, 2017

Gilligan 

A wack gangster. Popularized by Milk from the YT channel ItzmilkTV.
Tommy: Man CJ been fuckin up it might be time for another DP.

Tiny Loc: Yee dat foo been actin real gilligan lately i think its time for a checkup.
Gilligan by Drock666 May 4, 2022

Gilligan Gay 

When a man is not really gay but is extremely awkward around women, becoming nervous, tongue-tied etc. like the way Gilligan would react to Ginger on "Gilligan's Island"
Last night at the bar this really hot chick was hitting on my friend Steve, but he got all Gilligan Gay on her and totally blew it.
Gilligan Gay by Mr.Juan-derful January 3, 2010

Gilligan'd

To Be Stranded Somewhere By Any Extenuating Circumstance.
E.g. A Popped Tire, Flood Waters, Dead Battery or Incorrect Gas Gauge.

*Originated From The Old T.V. Show “Gilligan’s Island.”
Baron: Damn it, The Battery Is Dead.
Ryan: So....What Are You Telling Me?
Baron: Well...I’m Afraid We've Been Gilligan'd
Ryan: NOOOOOOO!!!!
The Professor: Its Not That Bad...I'll Get The Coconut Radio
Gilligan'd by Baron Mathot September 25, 2005

Gilligan's Island

n. A location that, although existing within the continental United States is sufficiently remote as to have no available Cell Phone or Internet service whatsoever.
Don't bother emailing me the changes tomorrow. We'll be camping in the Adirondacks so I'll be on "Gilligan's Island" until Sunday afternoon.
Gilligan's Island by tagz July 12, 2010